3,4-Dimethoxyaniline → 2-Cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl ester

HRID 132541Notes

Reaction equation

HRID 132541 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[NH2:6].[CH2:12]([O:14][C:15](=[O:23])[C:16](=[CH:19]OCC)[C:17]#[N:18])[CH3:13]>C1(C)C=CC=CC=1>[CH2:12]([O:14][C:15](=[O:23])[C:16]([C:17]#[N:18])=[CH:19][NH:6][C:5]1[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:13]

Participants

4

Reactant 2

HCID 227703,4-DimethoxyanilineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 691625702-Cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl esterYield 72.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

3,4-dimethoxyaniline (30.6 g, 200 mmol) was diluted with toluene (80 mL) and to the resultant solution was added ethyl(ethoxymethylene)cyanoacetate (33.8 g, 200 mmol). The resultant reaction was heated to 100° C. and allowed to stir at for 1 hour, then heated to 125° C. and allowed to stir for 15 minutes. The reaction mixture was cooled to room temperature and concentrated in vacuo to provide a crude residue, which was recrystallized from EtOAc to provide 2-cyano-3-(3,4-dimethoxyphenylamino)acrylic acid ethyl ester as a tan solid (40.0 g, 72%). mp 166-170° C.; MS (ES+) m/z 277.2 [M+H].

Workup

  1. customThe resultant reaction
  2. temperatureheated to 125° C.
  3. stirringto stir for 15 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. customto provide a crude residue, which
  7. customwas recrystallized from EtOAc

Sources & evidence

ORD record
ord-4fbbab148fed4b9991120d05bca3778d
Source dataset
uspto-grants-2008_06
Patent number
US07388016B2

Reaction notes

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